Chloroacetic Acid → 2-chloromethyl-4-phenyl-1H-benzimidazole

HRID 747291

Reaktionsgleichung

Reaktionsgleichung von HRID 747291
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]=1[N+:14]([O-])=O.[Cl:17][CH2:18][C:19](O)=O>CO.[Pd]>[Cl:17][CH2:18][C:19]1[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:3]=2[N:14]=1

Komponenten

5

Edukt 2

HCID 300Chloroacetic AcidHCID 105127972-Amino-6-phenyl-nitrobenzene2×

Produkt 1

HCID 220186182-chloromethyl-4-phenyl-1H-benzimidazoleAusbeute 92,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 2-amino-6-phenyl-nitrobenzene (0.600 g, 2.80 mmol) in MeOH (28 mL) was hydrogenated (30 psi) over palladium, 10 wt. % on activated carbon (0.121 g). The resultant crude 3-phenyl-1,2-phenylenediamine was reacted with chloroacetic acid (0.537 g, 5.68 mmol) in refluxing 4 N H1 (6 mL) overnight. After normal workup, 0.63 g (92%) of 2-chloromethyl-4-phenyl-1H-benzimidazole was isolated as a brown solid, which was used without further purification.

Aufarbeitung

  1. temperaturein refluxing 4 N H1 (6 mL) overnight

Quellen und Nachweise

ORD-Eintrag
ord-364db22dc4db460b9262e995d4ab8504
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396840B2

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